WO2009053545A3 - Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine - Google Patents

Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine Download PDF

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Publication number
WO2009053545A3
WO2009053545A3 PCT/FR2008/001146 FR2008001146W WO2009053545A3 WO 2009053545 A3 WO2009053545 A3 WO 2009053545A3 FR 2008001146 W FR2008001146 W FR 2008001146W WO 2009053545 A3 WO2009053545 A3 WO 2009053545A3
Authority
WO
WIPO (PCT)
Prior art keywords
synthesis
agomelatine
naphthyl
acetonitrile
methoxy
Prior art date
Application number
PCT/FR2008/001146
Other languages
French (fr)
Other versions
WO2009053545A2 (en
Inventor
Thierry Dubuffet
Jean-Pierre Lecouve
Jean-Paul Hermet
Original Assignee
Servier Lab
Thierry Dubuffet
Jean-Pierre Lecouve
Jean-Paul Hermet
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP08842551.7A priority Critical patent/EP2176214B1/en
Priority to BRPI0815126-1A2A priority patent/BRPI0815126A2/en
Application filed by Servier Lab, Thierry Dubuffet, Jean-Pierre Lecouve, Jean-Paul Hermet filed Critical Servier Lab
Priority to NZ583064A priority patent/NZ583064A/en
Priority to AU2008316406A priority patent/AU2008316406B2/en
Priority to CN200880101738XA priority patent/CN101772484B/en
Priority to US12/733,034 priority patent/US8252951B2/en
Priority to ES08842551.7T priority patent/ES2467690T3/en
Priority to KR1020107004649A priority patent/KR101179173B1/en
Priority to CA2695234A priority patent/CA2695234C/en
Priority to JP2010519488A priority patent/JP5250626B2/en
Priority to AP2010005145A priority patent/AP2611A/en
Priority to SI200831201T priority patent/SI2176214T1/en
Priority to DK08842551.7T priority patent/DK2176214T3/en
Priority to EA201000257A priority patent/EA016333B1/en
Priority to PL08842551T priority patent/PL2176214T3/en
Priority to RS20140155A priority patent/RS53250B/en
Publication of WO2009053545A2 publication Critical patent/WO2009053545A2/en
Publication of WO2009053545A3 publication Critical patent/WO2009053545A3/en
Priority to ZA2010/01184A priority patent/ZA201001184B/en
Priority to HK10112191.0A priority patent/HK1145830A1/en
Priority to US13/561,421 priority patent/US8436206B2/en
Priority to HRP20140407AT priority patent/HRP20140407T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to a method for the industrial synthesis of a compound of the formula (I). The invention can be used for the synthesis of agomelatine.
PCT/FR2008/001146 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine WO2009053545A2 (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
RS20140155A RS53250B (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
JP2010519488A JP5250626B2 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl) acetonitrile and its use in the synthesis of agomelatin
NZ583064A NZ583064A (en) 2007-08-03 2008-08-01 New process for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
AU2008316406A AU2008316406B2 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
CN200880101738XA CN101772484B (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine
US12/733,034 US8252951B2 (en) 2007-08-03 2008-08-01 Process for the synthesis of (methoxy-1-naphthyl) acetonitrile and application in the synthesis of agomelatine
ES08842551.7T ES2467690T3 (en) 2007-08-03 2008-08-01 New synthesis procedure for (7-methoxy-1-naphthyl) acetonitrile and its application to the synthesis of agomelatine
KR1020107004649A KR101179173B1 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of 7-methoxy-l-naphthylacetonitrile and application in the synthesis of agomelatine
SI200831201T SI2176214T1 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
EP08842551.7A EP2176214B1 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
AP2010005145A AP2611A (en) 2007-08-03 2008-08-01 New process for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesisof agomelatine
CA2695234A CA2695234C (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
DK08842551.7T DK2176214T3 (en) 2007-08-03 2008-08-01 New Process for the Synthesis of (7-Methoxy-1-Naphthyl) Acetonitrile and its Use in the Synthesis of Agomelatine
EA201000257A EA016333B1 (en) 2007-08-03 2008-08-01 Method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine
PL08842551T PL2176214T3 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
BRPI0815126-1A2A BRPI0815126A2 (en) 2007-08-03 2008-08-01 (7-METHOXY-L-NAPHYL) ACETONYTHRIL SYNTHESIS PROCESS AND APPLICATION TO AGOMELATIN SYNTHESIS
ZA2010/01184A ZA201001184B (en) 2007-08-03 2010-02-18 New process for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and application in the synthesis of agomelatine
HK10112191.0A HK1145830A1 (en) 2007-08-03 2010-12-29 Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine
US13/561,421 US8436206B2 (en) 2007-08-03 2012-07-30 Process for the synthesis of (7-methoxy-1-naphthyl) acetonitrile and application in the synthesis of agomelatine
HRP20140407AT HRP20140407T1 (en) 2007-08-03 2014-05-06 Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0705688 2007-08-03
FR0705688A FR2919606B1 (en) 2007-08-03 2007-08-03 NEW PROCESS FOR SYNTHESIZING (7-METHOXY-1-NAPHTHYL) ACETONITRILE AND APPLICATION TO THE SYNTHESIS OF AGOMELATIN

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/733,034 A-371-Of-International US8252951B2 (en) 2007-08-03 2008-08-01 Process for the synthesis of (methoxy-1-naphthyl) acetonitrile and application in the synthesis of agomelatine
US13/561,421 Division US8436206B2 (en) 2007-08-03 2012-07-30 Process for the synthesis of (7-methoxy-1-naphthyl) acetonitrile and application in the synthesis of agomelatine

Publications (2)

Publication Number Publication Date
WO2009053545A2 WO2009053545A2 (en) 2009-04-30
WO2009053545A3 true WO2009053545A3 (en) 2009-07-23

Family

ID=38926411

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2008/001146 WO2009053545A2 (en) 2007-08-03 2008-08-01 Novel method for the synthesis of (7-methoxy-l-naphthyl)acetonitrile and application in the synthesis of agomelatine

Country Status (35)

Country Link
US (2) US8252951B2 (en)
EP (1) EP2176214B1 (en)
JP (1) JP5250626B2 (en)
KR (1) KR101179173B1 (en)
CN (1) CN101772484B (en)
AP (1) AP2611A (en)
AR (1) AR070642A1 (en)
AU (1) AU2008316406B2 (en)
BR (1) BRPI0815126A2 (en)
CA (1) CA2695234C (en)
CL (1) CL2008002272A1 (en)
CY (1) CY1115094T1 (en)
DK (1) DK2176214T3 (en)
EA (1) EA016333B1 (en)
ES (1) ES2467690T3 (en)
FR (1) FR2919606B1 (en)
GE (1) GEP20125586B (en)
HK (1) HK1145830A1 (en)
HR (1) HRP20140407T1 (en)
JO (1) JO2992B1 (en)
MA (1) MA31740B1 (en)
MY (1) MY160226A (en)
NZ (1) NZ583064A (en)
PA (1) PA8792101A1 (en)
PE (1) PE20090881A1 (en)
PL (1) PL2176214T3 (en)
PT (1) PT2176214E (en)
RS (1) RS53250B (en)
SA (1) SA08290480B1 (en)
SI (1) SI2176214T1 (en)
TW (1) TWI352074B (en)
UA (1) UA94837C2 (en)
UY (1) UY31229A1 (en)
WO (1) WO2009053545A2 (en)
ZA (1) ZA201001184B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2580183B1 (en) 2010-06-10 2014-07-23 Gador S.A. New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide
WO2013054273A2 (en) 2011-10-11 2013-04-18 Ranbaxy Laboratories Limited Process for the preparation of agomelatine
CN103130673B (en) * 2011-11-28 2017-05-03 重庆医药工业研究院有限责任公司 Preparation method of agomelatine crystal type I
US20140336380A1 (en) 2011-12-01 2014-11-13 Ranbaxy Laboratories Limited Process for the preparation of agomelatine
ITMI20121444A1 (en) 2012-08-27 2014-02-28 Procos Spa PROCESS FOR AGOMELATINE PRODUCTION
CN104788342A (en) * 2015-04-07 2015-07-22 湖南大学 Method for preparing aromatic nitrile compound from aromatic methanol
CN107098828A (en) * 2017-05-09 2017-08-29 枣阳市残联福利生物化工厂 A kind of technique for efficiently synthesizing methoxynaphthalene acetonitrile
CN107382773A (en) * 2017-06-19 2017-11-24 太仓弘杉环保科技有限公司 A kind of method for synthesizing 7 methoxynaphthalene acetonitriles
CN107162933A (en) * 2017-06-19 2017-09-15 太仓大唐化纤厂 A kind of method for synthesizing the methoxynaphthalene acetonitrile of agomelatine important intermediate 7
CN107353229B (en) * 2017-08-08 2019-04-30 许昌恒生制药有限公司 A kind of preparation method of agomelatine intermediate body
CN112574065B (en) * 2020-12-30 2022-10-28 宁波职业技术学院 Preparation method of (benzene-1, 3, 5-triacyl) acetonitrile

Citations (2)

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Publication number Priority date Publication date Assignee Title
EP0709371A1 (en) * 1994-10-26 1996-05-01 Adir Et Compagnie O-arylmethyl N-(thio)acyl hydroxylamines as ligands for the melatonine receptors, their processes of preparation and the pharmaceutical compositions containing them
EP1564202A1 (en) * 2004-02-13 2005-08-17 Les Laboratoires Servier Novel process for synthesizing and a novel crystal form of agomelatin as well as pharmaceutical preparations containing these

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JPH02202864A (en) * 1989-01-31 1990-08-10 Hitachi Ltd 2,3-dicyano-6-naphthylmethanol derivative and production thereof
FR2658818B1 (en) 1990-02-27 1993-12-31 Adir Cie NOVEL DERIVATIVES WITH NAPHTHALENIC STRUCTURE, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
FR2696453B1 (en) * 1992-10-02 1994-12-23 Adir New arylalkyl (thio) amides, process for their preparation, and pharmaceutical compositions containing them.
FR2784375B1 (en) * 1998-10-12 2000-11-24 Adir NOVEL CYCLOALKYLENIC CHAIN DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
EP0709371A1 (en) * 1994-10-26 1996-05-01 Adir Et Compagnie O-arylmethyl N-(thio)acyl hydroxylamines as ligands for the melatonine receptors, their processes of preparation and the pharmaceutical compositions containing them
EP1564202A1 (en) * 2004-02-13 2005-08-17 Les Laboratoires Servier Novel process for synthesizing and a novel crystal form of agomelatin as well as pharmaceutical preparations containing these

Non-Patent Citations (2)

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Title
ARROWSMITH, G.B. ET. AL.: "Physical properties and chemical constitution. Part XLI. Naphthalene compounds", JOURNAL OF THE CHEMICAL SOCIETY, 1965, pages 2072 - 2078, XP002465456 *
SCHREIBER, KURT C. ET AL: "Conjugation in the naphthalene series. II. Solvolysis of x-methoxy-y-bromomethylnaphthalenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 84, 859-62 CODEN: JACSAT; ISSN: 0002-7863, 1962, XP002465455 *

Also Published As

Publication number Publication date
JP2010535746A (en) 2010-11-25
CL2008002272A1 (en) 2009-02-06
MA31740B1 (en) 2010-10-01
NZ583064A (en) 2011-07-29
ES2467690T3 (en) 2014-06-12
PA8792101A1 (en) 2009-09-17
US20100137628A1 (en) 2010-06-03
US8252951B2 (en) 2012-08-28
GEP20125586B (en) 2012-07-25
EP2176214A2 (en) 2010-04-21
KR20100039899A (en) 2010-04-16
SI2176214T1 (en) 2014-06-30
HRP20140407T1 (en) 2014-06-06
JO2992B1 (en) 2016-09-05
ZA201001184B (en) 2011-04-28
AU2008316406B2 (en) 2011-04-07
AR070642A1 (en) 2010-04-28
JP5250626B2 (en) 2013-07-31
US8436206B2 (en) 2013-05-07
WO2009053545A2 (en) 2009-04-30
CN101772484B (en) 2013-09-18
AP2611A (en) 2013-03-05
EA016333B1 (en) 2012-04-30
AP2010005145A0 (en) 2010-02-28
PE20090881A1 (en) 2009-07-18
TW200925141A (en) 2009-06-16
CN101772484A (en) 2010-07-07
UA94837C2 (en) 2011-06-10
PT2176214E (en) 2014-04-14
HK1145830A1 (en) 2011-05-06
US20120330062A1 (en) 2012-12-27
EA201000257A1 (en) 2010-08-30
BRPI0815126A2 (en) 2015-02-03
PL2176214T3 (en) 2014-06-30
CA2695234A1 (en) 2009-04-30
EP2176214B1 (en) 2014-03-05
FR2919606A1 (en) 2009-02-06
TWI352074B (en) 2011-11-11
CY1115094T1 (en) 2016-12-14
RS53250B (en) 2014-08-29
CA2695234C (en) 2013-02-05
MY160226A (en) 2017-02-28
FR2919606B1 (en) 2010-09-17
KR101179173B1 (en) 2012-09-03
SA08290480B1 (en) 2012-02-07
AU2008316406A1 (en) 2009-04-30
UY31229A1 (en) 2008-09-30
DK2176214T3 (en) 2014-06-10

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